Combining psychotherapy with psychopharmacology is a clinically challenging endeavor. In the psychopharmacology of the borderline patient, pills may function as transitional objects. This point is derived from a review of the literature, and illustrated by clinical material from three case studies. Recognition of the transitional properties of pills may aid therapists in making sense of many clinical phenomena and in developing effective treatment strategies. Other psychodynamic concepts may be useful in understanding the complex integration of psychotherapy and psychopharmacology.